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In the title compound, C
18H
26SO
7, the absolute configuration was confirmed as
S at all three chiral centres. Molecules are linked by three C—H
O contacts.
Supporting information
CCDC reference: 204671
Key indicators
- Single-crystal X-ray study
- T = 143 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.100
- Data-to-parameter ratio = 17.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.53
From the CIF: _reflns_number_total 4154
Count of symmetry unique reflns 2311
Completeness (_total/calc) 179.75%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1843
Fraction of Friedel pairs measured 0.797
Are heavy atom types Z>Si present yes
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
The title compound was synthesized starting from L-arabitol, as described by Holy (1982). Single crystals arose when the mother liquor was left undisturbed.
Methyl H atoms were identified in difference syntheses, idealized and then refined using rigid methyl groups (C—H = 0.98 Å and H—C—H = 109.5°) allowed to rotate but not tip. Other H atoms were included using a riding model, with C—H = 0.95 (sp2), 0.99 (methylene) or 1.00 Å (methine). The absolute configuration was based on 1849 Friedel pairs.
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
1-
O-
p-toluenesulfonyl-2,3:4,5-di-
O-isopropylidene-
L-arabitol
top
Crystal data top
C18H26O7S | F(000) = 412 |
Mr = 386.45 | Dx = 1.333 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9957 (10) Å | Cell parameters from 52 reflections |
b = 14.527 (3) Å | θ = 10–11.5° |
c = 8.3194 (14) Å | µ = 0.20 mm−1 |
β = 94.93 (2)° | T = 143 K |
V = 962.8 (3) Å3 | Plate, colourless |
Z = 2 | 0.7 × 0.5 × 0.15 mm |
Data collection top
Stoe DIF4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.4° |
Graphite monochromator | h = −10→10 |
ω/θ scans | k = −16→18 |
4605 measured reflections | l = −10→10 |
4154 independent reflections | 3 standard reflections every 60 min |
3891 reflections with I > 2σ(I) | intensity decay: 1.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2455P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4154 reflections | Δρmax = 0.23 e Å−3 |
240 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (7) |
Crystal data top
C18H26O7S | V = 962.8 (3) Å3 |
Mr = 386.45 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.9957 (10) Å | µ = 0.20 mm−1 |
b = 14.527 (3) Å | T = 143 K |
c = 8.3194 (14) Å | 0.7 × 0.5 × 0.15 mm |
β = 94.93 (2)° | |
Data collection top
Stoe DIF4 diffractometer | Rint = 0.018 |
4605 measured reflections | 3 standard reflections every 60 min |
4154 independent reflections | intensity decay: 1.3% |
3891 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.100 | Δρmax = 0.23 e Å−3 |
S = 1.04 | Δρmin = −0.24 e Å−3 |
4154 reflections | Absolute structure: Flack (1983) |
240 parameters | Absolute structure parameter: 0.01 (7) |
1 restraint | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5207 (3) | 0.79000 (15) | 0.8035 (2) | 0.0253 (4) | |
H1A | 0.4795 | 0.8518 | 0.8311 | 0.030* | |
H1B | 0.6448 | 0.7921 | 0.8082 | 0.030* | |
C2 | 0.4661 (3) | 0.72006 (14) | 0.9213 (2) | 0.0221 (4) | |
H2 | 0.5010 | 0.7409 | 1.0337 | 0.026* | |
C3 | 0.2790 (2) | 0.69517 (15) | 0.9078 (2) | 0.0225 (4) | |
H3 | 0.2320 | 0.7001 | 0.7928 | 0.027* | |
C4 | 0.1752 (3) | 0.75241 (15) | 1.0132 (3) | 0.0242 (4) | |
H4 | 0.2187 | 0.7469 | 1.1292 | 0.029* | |
C5 | −0.0122 (3) | 0.73407 (18) | 0.9925 (3) | 0.0321 (5) | |
H5A | −0.0475 | 0.7133 | 0.8814 | 0.039* | |
H5B | −0.0446 | 0.6869 | 1.0698 | 0.039* | |
O6 | −0.0839 (2) | 0.82085 (13) | 1.0249 (2) | 0.0417 (5) | |
O7 | 0.18521 (19) | 0.84537 (11) | 0.9597 (2) | 0.0312 (4) | |
O8 | 0.27746 (19) | 0.60195 (11) | 0.9579 (2) | 0.0341 (4) | |
O9 | 0.54235 (18) | 0.63342 (11) | 0.89318 (19) | 0.0259 (3) | |
C10 | 0.4464 (3) | 0.56617 (16) | 0.9697 (3) | 0.0262 (4) | |
C11 | 0.4485 (3) | 0.47753 (16) | 0.8754 (3) | 0.0314 (5) | |
H11A | 0.5621 | 0.4516 | 0.8859 | 0.038* | |
H11B | 0.4146 | 0.4898 | 0.7614 | 0.038* | |
H11C | 0.3702 | 0.4336 | 0.9177 | 0.038* | |
C12 | 0.5090 (3) | 0.55630 (19) | 1.1451 (3) | 0.0354 (5) | |
H12A | 0.5070 | 0.6165 | 1.1980 | 0.042* | |
H12B | 0.6242 | 0.5326 | 1.1533 | 0.042* | |
H12C | 0.4366 | 0.5134 | 1.1978 | 0.042* | |
C13 | 0.0348 (3) | 0.89175 (17) | 0.9939 (3) | 0.0298 (5) | |
C14 | 0.0641 (3) | 0.9499 (2) | 1.1433 (3) | 0.0405 (6) | |
H14A | 0.1401 | 1.0007 | 1.1227 | 0.049* | |
H14B | 0.1144 | 0.9121 | 1.2323 | 0.049* | |
H14C | −0.0432 | 0.9749 | 1.1722 | 0.049* | |
C15 | −0.0257 (4) | 0.9470 (2) | 0.8470 (3) | 0.0431 (6) | |
H15A | −0.0577 | 0.9052 | 0.7571 | 0.052* | |
H15B | 0.0643 | 0.9878 | 0.8176 | 0.052* | |
H15C | −0.1232 | 0.9839 | 0.8708 | 0.052* | |
O16 | 0.45175 (19) | 0.76403 (11) | 0.64149 (17) | 0.0258 (3) | |
O17 | 0.4286 (2) | 0.78277 (13) | 0.35815 (19) | 0.0368 (4) | |
O18 | 0.5789 (2) | 0.90040 (12) | 0.5278 (2) | 0.0339 (4) | |
S19 | 0.53854 (6) | 0.80636 (4) | 0.49578 (6) | 0.02601 (12) | |
C20 | 0.7248 (3) | 0.74269 (16) | 0.4949 (2) | 0.0257 (4) | |
C21 | 0.7229 (3) | 0.64848 (17) | 0.5190 (3) | 0.0323 (5) | |
H21 | 0.6218 | 0.6180 | 0.5398 | 0.039* | |
C22 | 0.8708 (3) | 0.59911 (18) | 0.5123 (3) | 0.0342 (5) | |
H22 | 0.8701 | 0.5343 | 0.5279 | 0.041* | |
C23 | 1.0205 (3) | 0.64290 (18) | 0.4831 (3) | 0.0313 (5) | |
C24 | 1.0180 (3) | 0.73729 (19) | 0.4593 (3) | 0.0354 (5) | |
H24 | 1.1190 | 0.7680 | 0.4392 | 0.042* | |
C25 | 0.8718 (3) | 0.78791 (17) | 0.4642 (3) | 0.0333 (5) | |
H25 | 0.8721 | 0.8525 | 0.4468 | 0.040* | |
C26 | 1.1808 (3) | 0.5895 (2) | 0.4795 (3) | 0.0410 (6) | |
H26A | 1.2607 | 0.6096 | 0.5684 | 0.049* | |
H26B | 1.2287 | 0.6003 | 0.3766 | 0.049* | |
H26C | 1.1576 | 0.5237 | 0.4911 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0284 (10) | 0.0224 (12) | 0.0251 (9) | −0.0039 (8) | 0.0022 (8) | −0.0008 (8) |
C2 | 0.0236 (10) | 0.0197 (11) | 0.0230 (9) | 0.0017 (7) | 0.0023 (7) | −0.0019 (7) |
C3 | 0.0218 (9) | 0.0179 (10) | 0.0281 (10) | 0.0011 (7) | 0.0038 (7) | −0.0009 (8) |
C4 | 0.0260 (10) | 0.0208 (11) | 0.0261 (10) | 0.0035 (8) | 0.0043 (8) | −0.0007 (8) |
C5 | 0.0274 (11) | 0.0277 (13) | 0.0422 (13) | 0.0005 (9) | 0.0090 (9) | −0.0028 (10) |
O6 | 0.0269 (8) | 0.0303 (11) | 0.0697 (12) | 0.0045 (7) | 0.0147 (8) | −0.0025 (8) |
O7 | 0.0262 (8) | 0.0199 (8) | 0.0488 (10) | 0.0040 (6) | 0.0105 (7) | −0.0018 (7) |
O8 | 0.0258 (8) | 0.0178 (8) | 0.0601 (11) | 0.0023 (6) | 0.0125 (7) | 0.0028 (7) |
O9 | 0.0252 (7) | 0.0193 (8) | 0.0341 (8) | 0.0033 (6) | 0.0082 (6) | 0.0009 (6) |
C10 | 0.0254 (10) | 0.0198 (11) | 0.0339 (11) | 0.0018 (8) | 0.0062 (8) | −0.0002 (8) |
C11 | 0.0349 (12) | 0.0215 (12) | 0.0382 (12) | 0.0035 (9) | 0.0048 (9) | −0.0040 (9) |
C12 | 0.0456 (14) | 0.0276 (12) | 0.0331 (12) | −0.0016 (10) | 0.0048 (10) | 0.0029 (10) |
C13 | 0.0263 (12) | 0.0241 (12) | 0.0400 (13) | 0.0059 (9) | 0.0080 (9) | −0.0017 (9) |
C14 | 0.0381 (13) | 0.0435 (16) | 0.0400 (14) | 0.0095 (11) | 0.0040 (10) | −0.0089 (11) |
C15 | 0.0439 (15) | 0.0460 (17) | 0.0391 (14) | 0.0131 (12) | 0.0016 (11) | 0.0020 (11) |
O16 | 0.0252 (7) | 0.0282 (8) | 0.0242 (7) | −0.0054 (6) | 0.0036 (6) | −0.0007 (6) |
O17 | 0.0335 (8) | 0.0485 (12) | 0.0280 (8) | 0.0004 (7) | 0.0001 (6) | 0.0055 (7) |
O18 | 0.0353 (8) | 0.0256 (9) | 0.0417 (9) | 0.0003 (7) | 0.0084 (7) | 0.0057 (7) |
S19 | 0.0257 (2) | 0.0269 (3) | 0.0256 (2) | −0.0007 (2) | 0.00322 (17) | 0.0038 (2) |
C20 | 0.0251 (10) | 0.0282 (12) | 0.0239 (10) | 0.0015 (8) | 0.0035 (7) | −0.0010 (8) |
C21 | 0.0304 (11) | 0.0288 (13) | 0.0383 (12) | −0.0034 (9) | 0.0059 (9) | 0.0039 (9) |
C22 | 0.0397 (12) | 0.0257 (12) | 0.0369 (12) | 0.0040 (9) | 0.0030 (10) | 0.0006 (10) |
C23 | 0.0312 (11) | 0.0352 (14) | 0.0270 (11) | 0.0032 (10) | 0.0004 (8) | −0.0079 (9) |
C24 | 0.0274 (11) | 0.0362 (14) | 0.0435 (13) | −0.0037 (10) | 0.0081 (9) | −0.0040 (11) |
C25 | 0.0316 (11) | 0.0303 (15) | 0.0389 (12) | −0.0038 (9) | 0.0086 (9) | 0.0001 (9) |
C26 | 0.0368 (13) | 0.0363 (15) | 0.0493 (15) | 0.0066 (11) | 0.0003 (11) | −0.0126 (11) |
Geometric parameters (Å, º) top
C1—O16 | 1.461 (2) | C12—H12C | 0.9800 |
C1—C2 | 1.502 (3) | C13—C14 | 1.505 (3) |
C1—H1A | 0.9900 | C13—C15 | 1.507 (3) |
C1—H1B | 0.9900 | C14—H14A | 0.9800 |
C2—O9 | 1.427 (2) | C14—H14B | 0.9800 |
C2—C3 | 1.533 (3) | C14—H14C | 0.9800 |
C2—H2 | 1.0000 | C15—H15A | 0.9800 |
C3—O8 | 1.417 (3) | C15—H15B | 0.9800 |
C3—C4 | 1.508 (3) | C15—H15C | 0.9800 |
C3—H3 | 1.0000 | O16—S19 | 1.5728 (15) |
C4—O7 | 1.426 (3) | O17—S19 | 1.4243 (17) |
C4—C5 | 1.517 (3) | O18—S19 | 1.4237 (19) |
C4—H4 | 1.0000 | S19—C20 | 1.754 (2) |
C5—O6 | 1.420 (3) | C20—C21 | 1.384 (3) |
C5—H5A | 0.9900 | C20—C25 | 1.389 (3) |
C5—H5B | 0.9900 | C21—C22 | 1.389 (3) |
O6—C13 | 1.439 (3) | C21—H21 | 0.9500 |
O7—C13 | 1.428 (3) | C22—C23 | 1.395 (4) |
O8—C10 | 1.443 (3) | C22—H22 | 0.9500 |
O9—C10 | 1.425 (3) | C23—C24 | 1.385 (4) |
C10—C12 | 1.508 (3) | C23—C26 | 1.501 (3) |
C10—C11 | 1.509 (3) | C24—C25 | 1.384 (3) |
C11—H11A | 0.9800 | C24—H24 | 0.9500 |
C11—H11B | 0.9800 | C25—H25 | 0.9500 |
C11—H11C | 0.9800 | C26—H26A | 0.9800 |
C12—H12A | 0.9800 | C26—H26B | 0.9800 |
C12—H12B | 0.9800 | C26—H26C | 0.9800 |
| | | |
O16—C1—C2 | 108.63 (16) | H12B—C12—H12C | 109.5 |
O16—C1—H1A | 110.0 | O7—C13—O6 | 106.13 (18) |
C2—C1—H1A | 110.0 | O7—C13—C14 | 110.81 (19) |
O16—C1—H1B | 110.0 | O6—C13—C14 | 108.2 (2) |
C2—C1—H1B | 110.0 | O7—C13—C15 | 107.91 (19) |
H1A—C1—H1B | 108.3 | O6—C13—C15 | 110.8 (2) |
O9—C2—C1 | 109.73 (17) | C14—C13—C15 | 112.8 (2) |
O9—C2—C3 | 102.01 (16) | C13—C14—H14A | 109.5 |
C1—C2—C3 | 116.63 (17) | C13—C14—H14B | 109.5 |
O9—C2—H2 | 109.4 | H14A—C14—H14B | 109.5 |
C1—C2—H2 | 109.4 | C13—C14—H14C | 109.5 |
C3—C2—H2 | 109.4 | H14A—C14—H14C | 109.5 |
O8—C3—C4 | 109.70 (17) | H14B—C14—H14C | 109.5 |
O8—C3—C2 | 103.71 (16) | C13—C15—H15A | 109.5 |
C4—C3—C2 | 114.18 (17) | C13—C15—H15B | 109.5 |
O8—C3—H3 | 109.7 | H15A—C15—H15B | 109.5 |
C4—C3—H3 | 109.7 | C13—C15—H15C | 109.5 |
C2—C3—H3 | 109.7 | H15A—C15—H15C | 109.5 |
O7—C4—C3 | 107.00 (17) | H15B—C15—H15C | 109.5 |
O7—C4—C5 | 102.24 (18) | C1—O16—S19 | 116.98 (12) |
C3—C4—C5 | 115.13 (19) | O18—S19—O17 | 119.73 (11) |
O7—C4—H4 | 110.7 | O18—S19—O16 | 109.80 (10) |
C3—C4—H4 | 110.7 | O17—S19—O16 | 104.05 (9) |
C5—C4—H4 | 110.7 | O18—S19—C20 | 109.15 (11) |
O6—C5—C4 | 103.50 (19) | O17—S19—C20 | 109.60 (11) |
O6—C5—H5A | 111.1 | O16—S19—C20 | 103.19 (9) |
C4—C5—H5A | 111.1 | C21—C20—C25 | 121.0 (2) |
O6—C5—H5B | 111.1 | C21—C20—S19 | 120.07 (17) |
C4—C5—H5B | 111.1 | C25—C20—S19 | 118.93 (18) |
H5A—C5—H5B | 109.0 | C20—C21—C22 | 119.0 (2) |
C5—O6—C13 | 108.55 (17) | C20—C21—H21 | 120.5 |
C4—O7—C13 | 108.30 (17) | C22—C21—H21 | 120.5 |
C3—O8—C10 | 109.42 (16) | C21—C22—C23 | 121.2 (2) |
C10—O9—C2 | 106.11 (16) | C21—C22—H22 | 119.4 |
O9—C10—O8 | 105.03 (17) | C23—C22—H22 | 119.4 |
O9—C10—C12 | 110.51 (18) | C24—C23—C22 | 118.3 (2) |
O8—C10—C12 | 109.35 (19) | C24—C23—C26 | 120.7 (2) |
O9—C10—C11 | 108.81 (18) | C22—C23—C26 | 121.0 (3) |
O8—C10—C11 | 108.91 (18) | C25—C24—C23 | 121.6 (2) |
C12—C10—C11 | 113.8 (2) | C25—C24—H24 | 119.2 |
C10—C11—H11A | 109.5 | C23—C24—H24 | 119.2 |
C10—C11—H11B | 109.5 | C24—C25—C20 | 118.9 (2) |
H11A—C11—H11B | 109.5 | C24—C25—H25 | 120.5 |
C10—C11—H11C | 109.5 | C20—C25—H25 | 120.5 |
H11A—C11—H11C | 109.5 | C23—C26—H26A | 109.5 |
H11B—C11—H11C | 109.5 | C23—C26—H26B | 109.5 |
C10—C12—H12A | 109.5 | H26A—C26—H26B | 109.5 |
C10—C12—H12B | 109.5 | C23—C26—H26C | 109.5 |
H12A—C12—H12B | 109.5 | H26A—C26—H26C | 109.5 |
C10—C12—H12C | 109.5 | H26B—C26—H26C | 109.5 |
H12A—C12—H12C | 109.5 | | |
| | | |
O16—C1—C2—O9 | 66.6 (2) | C4—O7—C13—C14 | 101.1 (2) |
O16—C1—C2—C3 | −48.7 (2) | C4—O7—C13—C15 | −134.9 (2) |
O9—C2—C3—O8 | 29.19 (19) | C5—O6—C13—O7 | −6.2 (2) |
C1—C2—C3—O8 | 148.71 (18) | C5—O6—C13—C14 | −125.2 (2) |
O9—C2—C3—C4 | 148.52 (17) | C5—O6—C13—C15 | 110.7 (2) |
C1—C2—C3—C4 | −92.0 (2) | C2—C1—O16—S19 | −160.18 (14) |
O8—C3—C4—O7 | 178.56 (17) | C1—O16—S19—O18 | −40.71 (17) |
C2—C3—C4—O7 | 62.7 (2) | C1—O16—S19—O17 | −170.00 (16) |
O8—C3—C4—C5 | −68.6 (2) | C1—O16—S19—C20 | 75.55 (17) |
C2—C3—C4—C5 | 175.52 (19) | O18—S19—C20—C21 | 158.93 (18) |
O7—C4—C5—O6 | −33.0 (2) | O17—S19—C20—C21 | −68.2 (2) |
C3—C4—C5—O6 | −148.65 (19) | O16—S19—C20—C21 | 42.2 (2) |
C4—C5—O6—C13 | 24.3 (2) | O18—S19—C20—C25 | −23.2 (2) |
C3—C4—O7—C13 | 151.62 (17) | O17—S19—C20—C25 | 109.67 (19) |
C5—C4—O7—C13 | 30.2 (2) | O16—S19—C20—C25 | −139.96 (18) |
C4—C3—O8—C10 | −133.01 (18) | C25—C20—C21—C22 | 0.1 (3) |
C2—C3—O8—C10 | −10.7 (2) | S19—C20—C21—C22 | 177.84 (18) |
C1—C2—O9—C10 | −161.76 (16) | C20—C21—C22—C23 | 0.5 (4) |
C3—C2—O9—C10 | −37.49 (19) | C21—C22—C23—C24 | −0.5 (4) |
C2—O9—C10—O8 | 31.7 (2) | C21—C22—C23—C26 | 178.7 (2) |
C2—O9—C10—C12 | −86.1 (2) | C22—C23—C24—C25 | 0.0 (4) |
C2—O9—C10—C11 | 148.19 (18) | C26—C23—C24—C25 | −179.2 (2) |
C3—O8—C10—O9 | −12.0 (2) | C23—C24—C25—C20 | 0.5 (4) |
C3—O8—C10—C12 | 106.6 (2) | C21—C20—C25—C24 | −0.5 (3) |
C3—O8—C10—C11 | −128.42 (19) | S19—C20—C25—C24 | −178.35 (18) |
C4—O7—C13—O6 | −16.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O17i | 1.00 | 2.48 | 3.396 (3) | 152 |
C15—H15C···O8ii | 0.98 | 2.61 | 3.509 (3) | 153 |
C24—H24···O17iii | 0.95 | 2.63 | 3.521 (3) | 156 |
Symmetry codes: (i) x, y, z+1; (ii) −x, y+1/2, −z+2; (iii) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C18H26O7S |
Mr | 386.45 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 143 |
a, b, c (Å) | 7.9957 (10), 14.527 (3), 8.3194 (14) |
β (°) | 94.93 (2) |
V (Å3) | 962.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.7 × 0.5 × 0.15 |
|
Data collection |
Diffractometer | Stoe DIF4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4605, 4154, 3891 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.100, 1.04 |
No. of reflections | 4154 |
No. of parameters | 240 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.01 (7) |
Selected torsion angles (º) topO9—C2—C3—O8 | 29.19 (19) | C3—C2—O9—C10 | −37.49 (19) |
O7—C4—C5—O6 | −33.0 (2) | C2—O9—C10—O8 | 31.7 (2) |
C4—C5—O6—C13 | 24.3 (2) | C3—O8—C10—O9 | −12.0 (2) |
C5—C4—O7—C13 | 30.2 (2) | C4—O7—C13—O6 | −16.1 (2) |
C2—C3—O8—C10 | −10.7 (2) | C5—O6—C13—O7 | −6.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O17i | 1.00 | 2.48 | 3.396 (3) | 152 |
C15—H15C···O8ii | 0.98 | 2.61 | 3.509 (3) | 153 |
C24—H24···O17iii | 0.95 | 2.63 | 3.521 (3) | 156 |
Symmetry codes: (i) x, y, z+1; (ii) −x, y+1/2, −z+2; (iii) x+1, y, z. |
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The title compound, (I), is a representative of a class of compounds important in the synthesis of polyhydroxyalkyl derivatives (Holy, 1978, 1982).
The molecule of (I) is shown in Fig. 1. The absolute configuration is confirmed as S at all three chiral centres C2, C3 and C4.
The conformation of the five-membered ring C2/C3/C10/O8/C9 is approximately twist (local diad through O9 and the midpoint of C3—O8) and that of C4/C5/C13/O6/C7 is approximately envelope (local mirror though C4 and the midpoint of C13—O6).
Molecules are linked by three C—H···O contacts that may be regarded as weak hydrogen bonds (Table 2); one, H4···O17, is much shorter than the others. The two contacts with purely translational symmetry operators link the molecules to form layers parallel to the xz plane at y ≈ 1/4, 3/4 (Fig. 2).